Category: pyridine-derivatives

Electric Literature of 175205-82-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 175205-82-0, name is 2-Bromo-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: A mixture of 2-bromo-3-(trifluoromethyl)pyridine (50 mg), 2-[4- (ethylsulfonyl)phenyl]-N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)phenyl]acetamide (104 mg), Cs2C03 (87 mg) and PdCl2(dppf)-CH2Cl2 adduct (10 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel and heated in the microwave at 100C for 30 mins. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford 2-[4-(ethylsulfonyl)phenyl]-N-{4-[3-(trifluoromethyl)-2- pyridinyl]phenyl}acetamide (32 mg) as a white solid. ‘H-NMR (400 MHz, DMSO-rf6) delta ppm 1.10 (t, J= 7.2 Hz, 3H), 3.28 (q, J= 7.2 Hz, 2H), 3.85 (s, 2H), 7.42 (d, J= 8.4 Hz, 2H), 7.62 (m, 3H), 7.70 (d, J= 8.4 Hz, 2H), 7.86 (d, J= 8.4 Hz, 2H), 8.28 (dd, = 1.2 Hz, 8.0 Hz, 1H), 8.89 (d, J= 4.4 Hz, 1H), 10.46 (s, 1H); 19F-NMR (376 MHz, DMSO-t?) delta ppm -55.98; MS(ES+) m/z 449 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65189-15-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 65189-15-3, name is 5,6-Dichloronicotinonitrile. A new synthetic method of this compound is introduced below.

Example 3 5-Chloro-2-methylthio-3-pyridinecarbonitrile STR11 5,6-Dichloro-3-pyridinecarbonitrile (1.73 g, 0.01 mol) was dissolved with stirring in dimethyl sulphoxide (25 mL) and sodium methanethiolate (0.77 g, 0.011 mol) added. The reaction mixture was stirred at room temperature for two hours and poured onto ice (100 g). The mixture was extracted with dichloromethane (50 mL), and the organic extract washed with water (100 mL), and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallisation of the residue from ethyl acetate:hexane gave the desired product (1.3 g, 71%) as a cream solid, MP 147-9 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65189-15-3, 5,6-Dichloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Kirby; Neil V.; Morrison; Irene M.; Canada; Emily J.; Pieczko; Mary E.; Gustafson; Gary D.; Cooper; David H.; Adamski; Jenifer L.; Mathieson; John T.; Galka; Christopher S.; US6133294; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 53937-02-3.

a) 8-(4-Benzyloxy)-2-oxopyridin-1(2H)-yl)-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one 8-Bromo-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (0.20 g, 0.68 mmol), 4-benzyloxy pyridinone (0.18 g, 0.89 mmol), and Cs2CO3 (0.24 g, 0.75 mmol) were suspended in DMSO (4.0 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar and the process repeated. 8-Hydroxyquinoline (30 mg, 0.21 mmol) and copper iodide (0.17 g, 0.89 mmol) were added to the suspension, and the evacuation/Ar flushing process was repeated twice more. The reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5:1 MeOH/NH4OH (10 mL), and the resulting solution was stirred at ambient temperature for 30 min. The reaction was further diluted with CH2Cl2 (75 mL). The solution was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with brine (3*25 mL). The organic solution was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 50:50 over 20 column volumes and held for 4 column volumes; increased to 0:100 over 10 column volumes) followed by flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 70:30 over 20 column volumes and held for 4 column volumes; increased to 25:75 over 10 column volumes) followed by trituration in hot EtOH provided the title compound (19 mg, 7%) as an off-white powder: mp 178-181 C.; 1H NMR (500 MHz, DMSO-d6) delta 8.29 (d, J=8.5 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.53 (t, J=5.5 Hz, 1H), 7.49-7.35 (m, 6H), 7.00 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 3.68 (s, 3H), 3.21-3.10 (m, 2H), 3.12 (t, J=6.5 Hz, 2H), 2.08-2.07 (m, 2H); ESI MS m/z 414 [M+H]+; HPLC (Method A) 97.2% (AUC), tR=16.5 min.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 625-92-3, 3,5-Dibromopyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C5H3Br2N, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3Br2N

[0187] Step 1. 3,5-Dibromoisonicotinaldehyde. Lithium diisopropylamide (507 mmol, 1.2 eq.) was added to 200 mL of dry THF at -78 C under N2. A solution of 3,5-dibromopyridine (100 g, 424 mmol) in 537 mL of dry THF was then added drop-wise over 30 mm. The reaction mixture was stirred at -78 C for 1 h. Ethyl formate (34.4 g, 465 mmol) was added drop-wise and stirred at -78 C for 30 mm, then the reaction mixture was poured into ice-cold saturated aqueous NaHCO3 solution. The mixture was extracted with 3 x 500 mL of EtOAc. The organic layer was concentrated to provide a brown solid, which was filtered through a pad of silica gel (eluted with dichloromethane) to give the title compound as a yellow powder (70 g, 63%).

The synthetic route of 625-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 73027-79-9

[00240] Step A: 6-Dichloro-4-(2-fluoro-4-iodophenylamino)nicotinic acid:[00241] To a solution of 2-fluoro-4-iodoaniline (11.3 g, 50.3 mmol) in 85 ml anhydrous THF is added LiHMDS (83 ml, 83 mmol, 1M/THF) over a period of 30 min at -78C. It is stirred for another 30 min, then a solution of methyl 4,6-dichloronicotinate (step B, example 9) (5.00 g, 26.2 mmol) in 85 ml THF is added dropwise. After complete addition the mixture is gradually allowed to warm to room temperature and stirred for another 18 hrs. It is quenched with H2O, then 1N HCl is added to (pH = 1) followed by brine. It is extracted using THF and dried with Na2SO4. The solvents are removed and the crude solid is suspended in300 ml of EtOAc. The suspension is heated with stirring at the reflux temperature for 5 min. It is cooled to room temperature and the precipitate is filtered and washed with EtOAc and dried at 50C for 5 h in oil pump vacuo.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 73027-79-9, 4,6-Dichloronicotinic acid.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159981-19-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde, molecular formula is C8H6F3NO2, molecular weight is 205.13, as common compound, the synthetic route is as follows.

Resin-bound tetra-alkylcyanoborohydride (9.03 g, 21.2 mmol) was added to a preformed mixture of 7-(benzylthio)-1,2,3,4-tetrahydroisoquinoline (4 g, 14.1 mmol), 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (3.18 g, 15.5 mmol), and glacial acetic acid (3.23 ml, 56.4 mmol) in MeOH (35 ml). The reaction vessel was fitted with a reflux condensor and heated to 40 C. overnight. The reaction mixture was cooled to room temperature, filtered through a fritted funnel, then neutralized by the addition of saturated aqueous NaHCO3 solution. The layers were cut and the aqueous phase extracted with EtOAc¡Á3. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography ?MPLC? (KP-Sil 100 g SNAP column, BIOTAGE system) eluting with 1% MeOH/DCM over 3 CV followed by a gradient of 6-9% MeOH/DCM over 8 CV to give the desired compound. LC/MS (m/z): 445 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 159981-19-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Berger, Richard; Blizzard, Timothy A.; Campbell, Brian T.; Chen, Helen Y.; Debenham, John S.; Dewnani, Sunita V.; Dubois, Byron; Gude, Candido; Guo, Zack Zhiqiang; Harper, Bart; Hu, Zhiyong; Lin, Songnian; Liu, Ping; Wang, Ming; Ujjainwalla, Feroze; Xu, Jiayi; Xu, Libo; Zhang, Rui; (64 pag.)US2018/9796; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17874-79-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, molecular formula is C8H7NO4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

10314] Dimethyl-2,5-pyridinedicarboxylate (960 mg, 4.9mmoles) and CaC12 (2.198 g, 19.7 mmoles) were added to a dried flask. THF (11 mE) and EtOH (12 mE) were added, and the resulting suspension was stirred on ice for 30 minutes. NaI3H4 (465 mg, 12.3 mmoles) was added portion wise with stirring. The reaction was allowed to come to room temperature overnight. Afier 18 h, the reaction was quenched by the dropwise addition of an aqueous solution of NH4C1 (saturated aqueous NH4C1 [20 mE] plus H20 [40 mE]) while stirring on ice. The aqueous layer was extracted with DCM (4×30 mE) and the combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the crude alcohol (678 mg) as a pale yellow solid. The crude alcohol was dissolved in dry DCM (45 mE), after which Dess-Martin periodinane (2.6 g, 6.1 mmoles) was added portion wise while stirring on ice. After 6 h, the reaction was quenched by the dropwise addition of a solution of 5% Na2S2O3 in half saturated NaHCO3 (80 mE). The aqueous layer was extracted with DCM (3×40 mE). The combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the title compound (504 mg, 62%) as a pale yellow solid. ?H NMR (400 MHz, CDC13) oe 10.16 (s, 1H), 9.38 (dd, J=0.5, 2.0 Hz, 1H), 8.49 (dd, J=2.0, 8.0 Hz, 1H), 8.05 (dd, J=0.5, 8.0 Hz, 1H), 4.02 (s, 1H); ?3C NMR (100 MHz, CDC13) oe 192.6, 164.8, 154.9, 151.2, 138.3, 121.1, 52.9; HRMS (El) mlz 165.0415 [calc?d for C8H7N03 (M) 165.042 1]

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17874-79-2, 5-(Methoxycarbonyl)picolinic acid.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; RAINES, Ronald T.; Vasta, James; (50 pag.)US2016/280701; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 2: Synthesis of tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate 10% palladium/carbon catalyst (0.50 g) was added to a solution of tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (2.85 g, 9.24 mmoL) in methanol (150 mL). The mixed solution was stirred under a hydrogen atmosphere (1 atm) at room temperature for 24 h, and filtered through Celite. The filtrate was concentrated under reduced pressure to obtain tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (2.12 g, yield: 82.5%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; WANG, Shulong; CHEN, Kuncheng; LIU, Xijie; HU, Yuandong; LIU, Bo; PENG, Yong; LUO, Hong; HAN, Yongxin; WANG, Shanchun; LIU, Mei; XU, Hongjiang; (38 pag.)EP3434676; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5345-47-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 5345-47-1, name is 2-Aminonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

(A) EtOH (500 mL) was added to 2-amino-nicotinic acid (25 g), followed by H2SO4 (25 mL, cone), and the mixture stirred at 75C overnight. The reaction mixture was then redissolved in H2O, neutralized with Na2CO3 (aq), and the resulting precipitate filtered and dried to provide 2-amino-nicotinic acid ethyl ester, which was used without further purification.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5345-47-1, 2-Aminonicotinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BUETTELMANN, Bernd; GOYAL, Bindu; PALMER, Wylie Solang; WO2010/97335; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131748-14-6, Adding some certain compound to certain chemical reactions, such as: 131748-14-6, name is 4-Chloro-(2-trifluoromethyl)pyridine,molecular formula is C6H3ClF3N, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 131748-14-6.

Example 2: Preparation of 2-[4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine hydrochloride To a solution of N-feri-butyloxycarbonyl-protected tyramine (130 g, 550 mmol), potassium carbonate (76 g, 550 mmol), and catalytic amounts of potassium iodide in N-methyl-2- pyrrolidone (NMP, 400 ml.) that was stirred for 10 minutes at room temperature was added 4- chloro-2-trifluoromethylpyridine (100 g, 550 mmol). The reaction mixture was then heated to 160C for 6 h, cooled, poured into water and extracted with methyl-feri-butylether (MTBE, 3x). The combined organic layers were washed with succesivly with 3 N NaOH and water, dried over Na2S04, and reduced in vacuo. The crude residue was purified by flash silica gel column chromatography to afford a 48% (102 g, 265 mmol) yield of N-tert-butyloxycarbonyl-protected 2-[4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine. To a solution of this material in dioxane (200 ml.) was added 4 M HCI in dioxane (250 ml_). The solution was left overnight to stir at room temperature, which resulted in precipitation of 2-[4-[[2-(trifluoromethyl)-4- pyridyl]oxy]phenyl]ethanamine hydrochloride. The reaction solution was evaporated and the residue was stirred with pentane and filtered to provide 100% (37 g, 104 mmol) of the desired amine hydrochloride.

According to the analysis of related databases, 131748-14-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MueLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/113787; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem